"De La Hoya has defeated 17 world champions and has won 10 world titles in six different weight classes. He has also generated more money than any other boxer in the history of the sport, an estimated $696 million pay-per-view income."

Tyson & Holyfield both made over $500 million Lewis made around $110 million... Lewis could have surpassed both if he had not turned down repeated career highest paydays throughout his career and chose to fight mediocre fighters instead of fighting the top fighters:

a lot of fighters have made a lot of money throughout their illustrious careers,that is why i believe in every era their have been a handful who have made a considerable amount more than their counterparts,we know that as the years go buy a marketable foe will be able to generate a much greater amount of income than previous foes due to the high demand in ppv buys and merchandising income,however there have been a lot of boxers from yesteryear who have made a lot of money due to their skills in the ring and their marketable ability outside the ring

Adjusted for inflaition, Naseem probably made more money than any fighter under 135. 12 million per fight as a freaking featherweight.

Lennox, Holyfield and Tyson averaged 20 mill fighting each other...

Louis and Dempsey probably made the most pre-1950.

Overall: Tyson, De La Hoya and Mayweather made the most overall.

When you do that, Leonard and Ali have to be included. Both Ali and Frazier were paid 2.5 million in 71 which was unreal of at that time. And Leonard made 40,000 for his pro debut which was unheard of in 1976. And Delahoya's paychecks were through the roof. In terms of overall money, he's the King.